L-Glutamic acid dimethyl ester hydrochloride
[CAS# 23150-65-4]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Glutamic acid derivative
• Name: L-Glutamic acid dimethyl ester hydrochloride
• Synonyms: Dimethyl L-2-aminoglutarate hydrochloride
• Molecular Formula: C₇H₁₃NO₄.HCl
• Molecular Weight: 211.64
• Protein Sequence: X
• CAS Registry Number: 23150-65-4
• EC Number: 245-461-0
• SMILES: COC(=O)CC[C@@H](C(=O)OC)N.Cl

Properties

• Melting pint: 89-90 °C (Expl.)
• alpha: 26 ° (c=5% in H2O) (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

L-Glutamic acid dimethyl ester hydrochloride is an esterified derivative of the amino acid L-glutamic acid, commonly used in organic synthesis, biochemical research, and pharmaceutical applications. The compound was developed as a way to modify L-glutamic acid, creating a more reactive form that facilitates the incorporation of glutamate structures into larger molecules. By converting the amino acid into its dimethyl ester form, researchers can take advantage of the increased solubility and reactivity of the compound, enabling new synthetic pathways that are useful for both research and industrial purposes.

One of the main applications of L-glutamic acid dimethyl ester hydrochloride is as a protected form of glutamate that can be readily integrated into peptide synthesis and other biochemical processes. When incorporated into peptides or proteins, this modified glutamic acid derivative can improve the overall stability and solubility of the compounds, particularly in environments where glutamate would otherwise be reactive or susceptible to hydrolysis. This makes the compound valuable in studies on neurotransmitter behavior and in drug development aimed at the central nervous system, where glutamate receptors play a key role in signal transduction and synaptic plasticity.

L-Glutamic acid dimethyl ester hydrochloride is also used in pharmacology and medicinal chemistry, particularly in the synthesis of prodrugs. The ester group increases the lipophilicity of the molecule, facilitating its passage across cell membranes. Once inside the target cell, esterases can hydrolyze the ester bonds, releasing the active L-glutamic acid. This property is advantageous in drug delivery systems, as it enables controlled release of glutamic acid or its derivatives at the desired site of action, improving the bioavailability of certain drugs and minimizing side effects.

The compound further serves as a precursor in synthesizing glutamate analogs and derivatives for use in enzyme inhibition studies, where modified glutamate compounds can mimic or block natural substrates of glutamate-processing enzymes. Such research has implications in the treatment of diseases where glutamate metabolism is disrupted, including certain neurodegenerative disorders and metabolic syndromes. As an effective means of modifying and studying glutamate function, L-glutamic acid dimethyl ester hydrochloride remains a valuable tool in biochemical research and drug development.

References

2023. Formation of quasi-stable nanostructures from L-N-stearoyl glutamic acid and its dimethyl ester on solid surfaces. *Journal of Nanoparticle Research*, 25(4).
DOI: 10.1007/s11051-023-05723-4

2021. Stereochemical aspects in the synthesis of novel N-(purin-6-yl)dipeptides as potential antimycobacterial agents. *Amino Acids*, 53(3).
DOI: 10.1007/s00726-021-02958-0

2019. Synthesis of Purine and 2-Aminopurine Conjugates with N-(4-Aminobenzoyl)-(S)-glutamic Acid. *Russian Journal of Organic Chemistry*, 55(6).
DOI: 10.1134/s1070428019060034